The subject of the invention is a composition for the oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, comprising at least one oxidation base and, as coupler, at least one 2-acylaminophenol of formula (I) comprising at least one cationic group Z of formula (II), their use as coupler for the oxidation dyeing of keratinous fibres, oxidation dyeing methods using them, as well as novel cationic 2-acylaminophenols of formula (Ixe2x80x2).
It is known to dye keratinous fibres and in particular human hair with dyeing compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, combined with oxidizing products, can give rise, through a process of oxidative condensation, to coloured or colouring compounds.
It is also known that it is possible to vary the shades obtained with these oxidation bases by combining them with couplers or colour modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules used in oxidation bases and couplers allows a rich palette of colours to be obtained.
The so-called xe2x80x9cpermanentxe2x80x9d colour obtained using these oxidation dyes must moreover satisfy a number of requirements. Thus, it must be without drawbacks from the toxicological point of view, it must make it possible to obtain shades in the desired intensity and exhibit good resistance towards external agents (light, adverse weather conditions, washing, permanent waving, perspiration, rubbing).
The dyes must also make it possible to cover grey hair and must finally be the least selective possible, that is to say make it possible to obtain the smallest possible differences in colour right along the same keratinous fibre, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
To obtain red shades, 4-aminophenol is generally used, alone or as a mixture with other bases, and in combination with appropriate couplers, and to obtain blue shades, para-phenylenediamines are normally used. The use of couplers derived from meta-phenylenediamines, in combination with derivatives of para-phenylenediamines, normally leads to blue shades whose fastness is generally poor.
It has already been proposed, in particular in patent FR-A-1,596,879, to use for the oxidation dyeing of keratinous fibres phenolic derivatives substituted at the 2-position with a ureinyl or thioureinyl radical, in combination with derivatives of para-phenylenediamines, in order to obtain shades similar to those obtained with the couplers derived from meta-phenylenediamines. However, the dyeing compositions containing the compounds mentioned in this patent generally lead, on the hair, to colours which are too selective and which lack intensity.
Moreover, it has already been proposed, in particular in patent BE 816,674, to use for the dyeing of keratinous fibres, in combination with derivatives of para-phenylenediamines, phenolic derivatives substituted at the 2-position with an acetyl or urea radical and at the 5-position with a halogen atom, in order to obtain colours ranging from green to green-blue. The fastness to light of the shades obtained on hair using these compositions is generally better than those obtained with dyeing compositions containing one or more meta-phenylenediamines as couplers. However, the fastness to adverse weather conditions and to washing as well as the intensities of the colours obtained are still too weak and constitute, in this respect, major disadvantages for persons skilled in the art.
In addition, there has already been proposed, in particular in patent application EP 0,579,204, to use for dyeing keratinous fibres, noncationic phenolic derivatives substituted at the 2-position with an acylamino, carbamoyl or ureyl radical, and at the 5-position with a C1-C4 alkyl radical, in combination with derivatives of para-phenylenediamine. However, the use of the phenolic derivatives mentioned in this European patent application does not make it possible to obtain a rich palette of colours, and, furthermore, the blue shades generally obtained are not completely satisfactory as regards their resistance to washing and to the action of light.
However, the applicant has now just discovered, completely unexpectedly and surprisingly, that the use, as coupler, of 2-acylaminophenols of formula (I) defined below and comprising at least one cationic group Z of formula (II) as defined below makes it possible to obtain dyeing compositions leading to intense colours in shades ranging from red to blue and exhibiting, furthermore, a remarkable fastness to light, adverse weather conditions, washing, perspiration or alternatively permanent waving.
These discoveries form the basis of the present invention.
The first subject of the invention is therefore a composition for the oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, characterized in that it contains, in a medium appropriate for dyeing:
at least one oxidation base, and
at least one coupler chosen from the compounds of the following formula (I) and their addition salts with an acid: 
xe2x80x83in which:
R1 represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 15 carbon atoms, linear or branched (it being possible for the branch(es) to form one or more carbon-containing rings comprising from 3 to 7 members) which may contain one or more double bonds and/or one or more triple bonds, (the said double bonds possibly leading to aromatic groups), in which one or more carbon atoms may be replaced by an oxygen, nitrogen or sulphur atom or by an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms; it being understood that the said SO2 group is not directly linked to the nitrogen atom at the 7-position carrying the radical R1; the said radical R1 comprising no peroxide bond or diazo, nitro or nitroso radicals;
R2 represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (it being possible for the branch(es) to form one or more carbon-containing rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups) and in which one or more carbon atoms may be replaced by an oxygen, nitrogen or sulphur atom or by an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms; the said radical R2 containing no peroxide bond or diazo, nitro or nitroso radicals; and it being understood that R2 cannot represent a hydroxyl or thio radical;
the radicals R1 and R2 may, in addition, be linked to form a saturated or unsaturated ring comprising from 5 to 7 members, consisting of carbon, nitrogen, oxygen, sulphur and/or of a Cxe2x95x90O group, each member being unsubstituted or substituted with one or two radicals R, which are identical or different, R being a C1-C6 alkyl radical, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 6 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), and in which one or more carbon atoms may be replaced by an oxygen, nitrogen or sulphur atom or by an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms; the said radical R containing no peroxide bond or diazo, nitro or nitroso radicals;
R3, R4 and R5, which are identical or different, represent a hydrogen or halogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), and in which one or more carbon atoms may be replaced by an oxygen, nitrogen or sulphur atom or by an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms; the said radicals R3, R4 and R5 comprising no peroxide bond or diazo, nitro or nitroso radicals; and it being understood that R5 cannot represent a hydroxyl, thio or amino radical or a substituted or unsubstituted sulphonylamino group; and it being understood that the radicals R3, R4 and R5 cannot be linked to the benzene ring of formula (I) by an xe2x80x94NHxe2x80x94NH-bond;
the radicals R1 and R3 may, in addition, be linked to form a saturated ring comprising from 6 to 7 members, consisting of carbon, nitrogen, oxygen, sulphur and/or of a Cxe2x95x90O group, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R having the same meanings as those indicated above; the said radical R comprising no peroxide bond or diazo, nitro or nitroso radicals;
the radicals R2 and R3 may also be linked to form a saturated ring comprising from 5 to 7 members, consisting of carbon, nitrogen, oxygen, sulphur and/or of a Cxe2x95x90O group, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R having the same meanings as those indicated above; the said radical R comprising no peroxide bond or diazo, nitro or nitroso radicals;
Y represents a hydrogen or halogen atom; a group xe2x80x94OR6, xe2x80x94SR6 or xe2x80x94NHxe2x80x94SO2R6 in which R6 represents a C1-C6 alkyl radical, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 6 members), unsubstituted or substituted with one or more radicals chosen from the group consisting of a halogen atom, a hydroxyl, C1-C4 alkoxy, amino and C1-C4 aminoalkyl radical; a phenyl radical which is unsubstituted or substituted with one or two radicals chosen from the group consisting of a C1-C4 alkyl, trifluoromethyl, carboxyl, C1-C4 alkoxycarbonyl, halogen, hydroxyl, C1-C4 alkoxy, amino and C1-C4 aminoalkyl radical; or a benzyl radical; and it being understood that Y cannot represent xe2x80x94NHxe2x80x94SO2R6 when R3 represents a hydroxyl radical;
Z is a cationic group represented by the following formula (II): 
xe2x80x83in which:
B represents a radical comprising from 1 to 15 carbon atoms, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds, the said double bonds possibly leading to aromatic groups, and in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 radical; and in which one or more carbon atoms may, independently of each other, be substituted with one or more halogen atoms or with one or more groups Z; the said radical B containing no peroxide bond or diazo, nitro or nitroso radicals;
D is chosen from the cationic groups of the following formulae (III) and (IV): 
xe2x80x83in which:
the radical B is linked to the group D by any one of the atoms of the radical D;
n and p can, independently of each other, take the value 0 or 1;
when n=0, then the group of formula (IV) can be linked to the compound of formula (I) directly by the nitrogen atom of the quaternary ammonium, in place of the radical R10;
Z1, Z2, Z3 and Z4, independently of each other, represent an oxygen atom; a sulphur atom; a nitrogen atom which is unsubstituted or substituted with a radical R11; or a carbon atom which is unsubstituted or substituted with one or two radicals R11, which are identical or different;
Z5 represents a nitrogen atom or a carbon atom which is unsubstituted or substituted with a radical R11;
Z6 can have the same meanings as those indicated below for the radical R11; it being understood that Z6 is different from a hydrogen atom;
xe2x80x83the radicals Z1 or Z5 can, in addition, form with Z6 a saturated or unsaturated ring comprising from 5 to 7 members, each member being unsubstituted or substituted with one or two radicals R11 which are identical or different;
R11 represents a hydrogen atom; a group Z; a radical comprising from 1 to 10 carbon atoms, linear or branched, which may contain one or more double bonds and/or one or more triple bonds, it being possible for the said double bonds to then possibly lead to aromatic groups, and in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom, or with an SO2 group, and in which one or more carbon atoms may, independently of each other, be substituted with one or more halogen atoms; the said radical containing no peroxide bond or diazo, nitro or nitroso radicals; it being possible, in addition, for two of the adjacent radicals Z1, Z2, Z3, Z4 and Z5 to form a ring comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R11 which are identical or different; a nitrogen atom which is unsubstituted or substituted with a radical R11; an oxygen atom; or a sulphur atom;
R7, R8, R9 and R10, which are identical or different, have the same meanings as those indicated above for the radical R11;
xe2x80x83it being possible for the radicals R7, R8 and R9 to also form, in pairs with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R11 which are identical or different; a nitrogen atom which is unsubstituted or substituted with a radical R11; an oxygen atom; or a sulphur atom;
Xxe2x88x92 represents an organic or inorganic anion and is preferably chosen from the group consisting of a halide group such as chloride, bromide, fluoride, iodide; a hydroxide; a sulphate; a hydrogen sulphate; a (C1-C6)alkyl sulphate such as for example a methyl sulphate or an ethyl sulphate; an acetate; a tartrate; an oxalate; a (C1-C6)alkyl sulphonate such as methyl sulphonate; an aryl sulphonate which is unsubstituted or substituted with a C1-C4 alkyl radical such as for example a 4-toluoyl sulphonate;
xe2x80x83it being understood that at least one of the groups R1 to R5 represents a group Z.
As indicated above, the oxidation dyeing composition containing the compound(s) of formula (I) in accordance with the invention makes it possible to obtain intense colours in shades ranging from red to blue and exhibiting, furthermore, a remarkable fastness to the various treatments to which the keratinous fibres may be subjected. These properties are particularly remarkable in particular as regards the resistance of the colours obtained to the action of light, adverse weather conditions, washing, permanent waving and perspiration.
According to the invention, and when it is indicated that one or more of the carbon atoms of the radical(s) R1 to R5 can be replaced by an oxygen, nitrogen or sulphur atom or by an SO2 group, and/or that the said radicals R1 to R5 may contain one or more double bonds and/or one or more triple bonds, that means that it is possible, by way of example, to make the following conversions: 
According to the invention, R1 preferably denotes a hydrogen atom, a radical Z; a group A1, A2, A3, A4 or A5, optionally separated from the nitrogen situated at the 7-position onto which the radical R1 is attached by a xe2x80x94(CO)xe2x80x94 group.
According to the invention, xe2x80x9cgroup A1xe2x80x9d is understood to mean a linear or branched C1-C8 alkyl radical which may carry one or two double bonds or one triple bond, which may be unsubstituted or substituted with a group chosen from a group A2, A4 and A5, which may be unsubstituted or substituted with one or two groups, which are identical or different, chosen from the Nxe2x80x94(C1-C3)alkylamino, Nxe2x80x94(C1-C3)alkyl-Nxe2x80x94(C1-C3)alkylamino, (C1-C6)alkoxy, oxo, alkoxycarbonyl, acyloxy, amide, acylamino, ureyl, sulphoxy, sulphonyl, sulphonamido, sulphonylamino, bromo, cyano and carboxyl groups, and which may be unsubstituted or substituted with one or more hydroxyl, fluoro or chloro groups.
xe2x80x9cGroup A2xe2x80x9d is understood to mean an aromatic group of the phenyl or naphthyl type, which may be unsubstituted or substituted with one to three groups, which are identical or different, chosen from the methyl, trifluoromethyl, ethyl, isopropyl, butyl, pentyl, fluoro, chloro, bromo, methoxy, trifluoromethoxy, ethoxy, propyloxy, acetyloxy, acetyl and cyano groups.
xe2x80x9cGroup A3xe2x80x9d is understood to mean heteroaromatic groups chosen from the furanyl, thiophenyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, isoxazolyl, isothiazolyl, pyrazolyl, pyrazolotriazolyl, pyrazoloimidazolyl, pyrrolotriazolyl, pyrazolopyrimidyl, pyrazolopyridyl, pyridyl, pyrimidyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, indolyl, indolidinyl, isoindolyl, indazolyl, benzotriazolyl, quinolinyl, benzoimidazolyl and benzopyrimidyl groups, the said groups being unsubstituted or substituted with 1 to 3 radicals chosen from a linear or branched C1-C4 alkyl radical, a C1-C4 monohydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a carboxyl radical, an alkoxycarbonyl radical, a halogen atom, an amido radical, an amino radical and a hydroxyl radical.
xe2x80x9cGroup A4xe2x80x9d is understood to mean a C3-C7 cycloalkyl radical, a norbonyl radical, carrying or otherwise a double bond and unsubstituted or substituted with 1 or 2 radicals chosen from a linear or branched C1-C4 alkyl radical, a C1-C4 monohydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a carboxyl radical, an alkoxycarbonyl radical, a halogen atom, an amido radical, an amino radical and a hydroxyl radical.
xe2x80x9cGroup A5xe2x80x9d is understood to mean a heterocycle chosen from the dihydrofuranyl, tetrahydrofuranyl, butyrolactonyl, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrothiophenonyl, iminothiolane, dihydropyrrolyl, pyrrolidinyl, pyrrolidinonyl, imidazolidinonyl, imidazolidinethionyl, oxazolidinyl, oxazolidinonyl, oxazolanethione, thiazolidinyl, isothiazolonyl, mercaptothiazolinyl, pyrazolidinonyl, iminothiolane, dioxolanyl, pentalactone, dioxanyl, dihydropyridinyl, piperidinyl, pentalactam, morpholinyl, pyrazoli(di)nyl, pyrimi(di)nyl, pyrazinyl, piperazinyl and azepinyl rings.
Among these substituents, R1 represents more particularly a hydrogen atom; a methyl, ethyl, isopropyl, allyl, phenyl, benzyl, fluorobenzyl, hydroxybenzyl, difluorobenzyl, trifluorobenzyl, chlorobenzyl, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy)benzyl, 3,4-methylenedioxybenzyl, 6-chloropiperonyl, 4-methylthiobenzyl, 4-methylsulphonylbenzyl, 4-acetylaminobenzyl, 4-carboxybenzyl, 1-naphthomethyl or 2-naphthomethyl radical; or a 2-hydroxyethyl, 2-methoxyethyl or 2-ethoxyethyl group.
Still more preferably, R1 represents a hydrogen atom or a methyl radical.
According to the invention, R2 preferably denotes a hydrogen atom, an amino group; a group Z; a group A1, A2, A3, A4 or A5 as defined above, optionally separated from the carbon (at the 8-position) with respect to the amide function of the compound of formula (I) by a group xe2x80x94Oxe2x80x94, xe2x80x94NH, xe2x80x94N(C1-C3)alkyl-, xe2x80x94(CO)xe2x80x94, xe2x80x94(CO)Oxe2x80x94 or xe2x80x94(CO)NHxe2x80x94.
Among these substituents, R2 preferably denotes a group Z; a radical chosen from the group (G1) consisting of a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclopentylmethyl, 3-cyclopentylpropyl, cyclohexyl, 2-cyclohexylethyl, norborn-2-yl, vinyl, 1-methylvinyl, 2-methylvinyl, 2,2-dimethylvinyl, allyl, 3-butenyl, phenyl, methylphenyl, dimethylphenyl, 2,4,6-trimethylphenyl, 4-ethylphenyl, (trifluoromethyl)phenyl, hydroxyphenyl, methoxyphenyl, ethoxyphenyl, acetoxyphenyl, (trifluoromethoxy)phenyl, aminophenyl, 4-dimethylaminophenyl, fluorophenyl, difluorophenyl, fluoro(trifluoromethyl)phenyl, chlorophenyl, dichlorophenyl, bromophenyl, naphth-1-yl, naphth-2-yl, (2-methoxy)naphth-1-yl, benzyl, 4xe2x80x2-methoxybenzyl, 2xe2x80x2,5xe2x80x2-dimethoxybenzyl, 3xe2x80x2,4xe2x80x2-dimethoxybenzyl, 4xe2x80x2-fluorobenzyl, 4xe2x80x2-chlorobenzyl, phenethyl, 2-phenylvinyl, (1-naphthyl)methyl, (2-naphthyl)methyl; tetrahydrofuran-2-yl, furan-2-yl, 5-methyl-2-(trifluoromethyl)furan-3-yl, 2-methyl-5-phenylfuran-3-yl, thiophen-2-yl, (thiophen-2-yl)methyl, 3-chlorothiophen-2-yl, 2,5-dichlorothiophen-3-yl, benzothiophen-2-yl, 3-chlorobenzothiophen-2-yl, isoxazol-5-yl, 5-methylisoxazol-3-yl, 3,5-dimethylisoxazol-4-yl, 1,3-dimethylpyrazol-5-yl, 1-ethyl-3-methylpyrazol-5-yl, 1-tert-butyl-3-methylpyrazol-5-yl, 3-tert-butyl-1-methylpyrazol-5-yl, 4-bromo-1-ethyl-3-methylpyrazol-5-yl, indol-3-ylcarboxyl, pyridinyl, chloropyridinyl, dichloropyridinyl, 5-(bromo)pyridin-3-yl, piperazin-2-yl, quinoxal-2-yl, fluoromethyl, difluoromethyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, heptafluoropropyl, 1,1,2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl, chloromethyl, chloroethyl, 1,1-dimethyl-2-chloroethyl, 1,2-dichloroethyl, 1-chloropropyl, 3-chloropropyl, 4-chlorobutyl, hydroxymethyl, methoxymethyl, phenoxymethyl, (4-chlorophenoxy)methyl, benzyloxymethyl, acetoxymethyl, 1,2-dihydroxyethyl, 1-phenoxyethyl, 1-acetoxyethyl, 2-(2-carboxyethoxy)ethyl, 1-phenoxyethyl, 1-acetoxyethyl, methoxycarbonyl, ethoxycarbonyl, (methoxycarbonyl)methyl, 2-carboxyethyl, 2-(methoxycarbonyl)ethyl, 2-carboxycyclopropyl, 2-carboxycyclohexane, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, neopentoxy, hexyloxy, cyclopentyloxy, cyclohexyloxy, vinyloxy, allyloxy, propargyloxy, chloromethoxy, 1-chloroethoxy, 2-methoxyethoxy, 4-chlorobutoxy, phenoxy, 4-methylphenoxy, 4-fluorophenoxy, 4-bromophenoxy, 4-chlorophenoxy, 4-methoxyphenoxy, naphth-2-yloxy, benzyloxy; amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, cyclohexylamino, allylamino, 2-chloroethylamino, 3-chloropropylamino, carboxymethylamino, phenylamino, fluorophenylamino, (trifluoromethyl)phenylamino, chlorophenylamino, bromophenylamino, 4-acetylphenylamino, methoxyphenylamino, (trifluoromethoxy)phenylamino, naphth-1-ylamino, benzylamino, phenethylamino, pyrid-3-ylamino, dimethylamino, 1-pyrrolidinyl and 4-morpholinyl radical.
When R1 and R2 form a ring, the said ring is preferably chosen from the 2-pyrrolidinon-1-yl, methyl-2-pyrrolidinon-1-yl, 5-carboxy-2-pyrrolidinon-1-yl, 5-methoxycarbonyl-2-pyrrolidinon-1-yl, pyrazolinon-1-yl, succinimid-1-yl, 3,5-diketopyrazolidin-1-yl, oxindolin-1-yl, maleimid-1-yl, isoindole-1,3-dion-2-yl, 2-piperidinon-1-yl and glutarimid-1-yl groups.
Still more preferably, R2 represents a radical chosen from the group (G2) consisting of a methyl, ethyl, propyl, allyl, phenyl, tetrahydrofuran-2-yl, furan-2-yl, thiophen-2-yl, pyridinyl, piperazin-2-yl, fluoromethyl, chloromethyl, 2-chloroethyl, methoxymethyl, acetoxymethyl, 1,2-dihydroxyethyl, methoxycarbonyl, 2-carboxyethyl, methoxy, ethoxy, propoxy, allyloxy, 2-chloroethoxy, 2-methoxyethoxy, amino, ethylamino, allylamino, 2-chloroethylamino, pyridylamino, dimethylamino, 1-pyrrolidinyl or 4-morpholinyl radical; or a group xe2x80x94D1, xe2x80x94Exe2x80x94D1, xe2x80x94Oxe2x80x94Exe2x80x94D1, xe2x80x94NHxe2x80x94Exe2x80x94D1, in which xe2x80x94Exe2x80x94 represents a xe2x80x94(CH2)qxe2x80x94 arm, q being an integer equal to 1 or 2, and D1 represents a group Dxe2x80x2 chosen from the 3-methylimidazolidinium-1-yl, 3-(2-hydroxyethyl)imidazolidinium-1-yl, 1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, N-(C1-C4)alkylpyridinium-2-yl, N-(C1-C4)alkylpyridinium-3-yl, N-(C1-C4)alkylpyridinium-4-yl, N-(2-hydroxyethyl)pyridinium-2-yl, N-(2-hydroxyethyl)pyridinium-3-yl, N-(2-hydroxyethyl)pyridinium-4-yl, pyridinium-1-yl, tri(C1-C4)alkylammonium-N-yl, 1-methylpiperidinium-1-yl and 1,4-dimethylpiperazinium-1-yl groups.
Still more preferably, R2 represents a methyl, methoxymethyl, 2-carboxyethyl, methoxy, amino, ethylamino or 1-pyrrolidinyl radical; a group xe2x80x94D1, xe2x80x94Exe2x80x94D1, xe2x80x94Oxe2x80x94Exe2x80x94D1 or xe2x80x94NHxe2x80x94Exe2x80x94D1, in which xe2x80x94Exe2x80x94 represents a xe2x80x94(CH2)qxe2x80x94 arm, q=1 to 2 and D1 a group Dxe2x80x2 as defined below.
According to the invention, R3 and R4, which are identical or different, preferably denote a hydrogen or halogen atom; a hydroxyl or amino group; a group Z; a group A1, A4 or A5 as defined above; a group A1, A2, A3, A4 or A5 as defined above and separated from the phenolic ring of the formula (I) by an oxygen atom or by a group xe2x80x94NHxe2x80x94, xe2x80x94N(C1-C3)alkyl-, xe2x80x94O(CO)xe2x80x94, xe2x80x94NH(CO)xe2x80x94, xe2x80x94N(C1-C3)alkyl(CO)xe2x80x94, xe2x80x94NH[Cxe2x95x90NH]xe2x80x94, xe2x80x94NH(CO)NHxe2x80x94, xe2x80x94NH(CO)N(C1-C3)alkyl-, xe2x80x94NH(CO)Oxe2x80x94, xe2x80x94NHSO2xe2x80x94, xe2x80x94NHSO2NHxe2x80x94 or xe2x80x94NHSO2N(C1-C3)alkyl-.
Among these substituents, R3 represents still more preferably a hydrogen or chlorine atom; a group Z; a methyl, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl, hydroxyl, methoxy, acetoxy, amino, methylamino or 2-hydroxyethylamino radical; a group xe2x80x94NH(CO)R12 in which R12 represents one of the radicals listed in the group (G1) as defined above; a group xe2x80x94NHSO2R13, in which R13 represents one of the radicals listed in the group (G3) consisting of the methyl, trifluoromethyl, ethyl, 2-chloroethyl, propyl, 3-chloropropyl, isopropyl, butyl, thiophen-2-yl, hydroxyl, ethoxy and dimethylamino radicals.
When R1 and R3 form a ring, together with the nitrogen atom at the 7-position of the compound of formula (I), the xe2x80x94CH2CH2CH2xe2x80x94 linkage is preferred for xe2x80x94R1R3xe2x80x94.
When R2 and R3 form a ring, together with the nitrogen atom at the 7-position of the compound of formula (I), the xe2x80x94CH2xe2x80x94, xe2x80x94C(CH3)2xe2x80x94 or xe2x80x94CH2CH2xe2x80x94 linkages are preferred for xe2x80x94R2R3xe2x80x94.
Still more preferably, R3 represents a hydrogen atom; a methyl, hydroxymethyl, aminomethyl, hydroxyl, methoxy, amino or methylamino radical; a methanesulphonylamino group; ethanesulphonylamino; dimethylaminosulphonylamino; a group xe2x80x94NH(CO)R14 in which R14 represents one of the radicals listed in the group (G2) as defined above; or a group xe2x80x94Oxe2x80x94Exe2x80x94D2, xe2x80x94NHxe2x80x94Exe2x80x94D2, xe2x80x94CH2Oxe2x80x94Exe2x80x94D2, xe2x80x94CH2NHxe2x80x94Exe2x80x94D2, xe2x80x94CH2NH(CO)xe2x80x94D2, xe2x80x94NH(CO)xe2x80x94D2, xe2x80x94NH(CO)xe2x80x94Exe2x80x94D2, xe2x80x94NH(CO)Oxe2x80x94Exe2x80x94D2, xe2x80x94NH(CO)NHxe2x80x94Exe2x80x94D2 or xe2x80x94NH(SO2)xe2x80x94Exe2x80x94D2, in which xe2x80x94Exe2x80x94 has the same meaning as that indicated above and D2 represents a group Dxe2x80x2 as defined above.
Among these substituents, R4 preferably represents a hydrogen or chlorine atom; a group Z; a methyl, ethyl, hydroxymethyl, methoxymethyl, aminomethyl, methylaminomethyl, hydroxyl, methoxy, acetoxy, amino, methylamino, N-piperidino or N-morpholino radical; a group xe2x80x94NH(CO)R15 in which R15 represents one of the radicals listed in the group (G1) defined above; or a group xe2x80x94NHSO2R16 in which R16 represents one of the radicals listed in the group (G3) defined above.
Still more preferably, R4 represents a hydrogen or chlorine atom; a methyl, hydroxymethyl, aminomethyl, hydroxyl, methoxy, amino or methylamino radical; a methanesulphonylamino group; ethanesulphonylamino; dimethylaminosulphonylamino; a group xe2x80x94NH(CO)R17 in which R17 represents one of the radicals listed in the group (G2) defined above; or a group xe2x80x94Oxe2x80x94Exe2x80x94D3, xe2x80x94NHxe2x80x94Exe2x80x94D3, xe2x80x94CH2Oxe2x80x94Exe2x80x94D3, xe2x80x94CH2NHxe2x80x94Exe2x80x94D3, xe2x80x94CH2NH(CO)xe2x80x94D3, xe2x80x94NH(CO)xe2x80x94D3, xe2x80x94NH(CO)xe2x80x94Exe2x80x94D3, xe2x80x94NH(CO)Oxe2x80x94Exe2x80x94D3, xe2x80x94NH(CO)NHxe2x80x94Exe2x80x94D3 or xe2x80x94NH(SO2)xe2x80x94Exe2x80x94D3, in which xe2x80x94Exe2x80x94 has the same meaning as indicated above, and D3 represents a group Dxe2x80x2 as defined above.
According to the invention, R5 is preferably chosen from a hydrogen or halogen atom; a group Z; a group A1, A4 or A5 as defined above; a group A1, A2, A3, A4 or A5 as defined above and separated from the phenolic ring of the compounds of formula (I) by an oxygen or sulphur atom or by a group xe2x80x94NHxe2x80x94, xe2x80x94N(C1-C3)alkyl-, xe2x80x94O(CO)xe2x80x94, xe2x80x94NH(CO)xe2x80x94, xe2x80x94N(C1-C3)alkyl(O)xe2x80x94, xe2x80x94NH[Cxe2x95x90NH]xe2x80x94, xe2x80x94NH(CO)NHxe2x80x94, xe2x80x94NH(CO)N(C1-C3)alkyl-, or xe2x80x94NH(CO)Oxe2x80x94.
Among these substituents, R5 preferably represents a hydrogen, chlorine, fluorine or bromine atom; a group Z; a methyl, trifluoromethyl, allyl, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl, methoxy, acetoxy or methylamino radical; or a group xe2x80x94NH(CO)R18 in which R18 represents one of the radicals listed in the group (G1) defined above.
Still more preferably, R5 represents a hydrogen, chlorine or fluorine atom; a methyl, hydroxymethyl, aminomethyl, methoxy or methylamino radical; a group xe2x80x94NH(CO)R19 in which R19 represents one of the radicals listed in the group (G2) defined above; or a group xe2x80x94Oxe2x80x94Exe2x80x94D4, xe2x80x94NHxe2x80x94Exe2x80x94D4, xe2x80x94CH2Oxe2x80x94Exe2x80x94D4, xe2x80x94CH2NHxe2x80x94Exe2x80x94D4, xe2x80x94CH2NH(CO)xe2x80x94D4, xe2x80x94NH(CO)xe2x80x94D4, xe2x80x94NH(CO)xe2x80x94Exe2x80x94D4, xe2x80x94NH(CO)Oxe2x80x94Exe2x80x94D4, or xe2x80x94NH(CO)NHxe2x80x94Exe2x80x94D4, in which xe2x80x94Exe2x80x94 has the same meaning as that indicated above, and D4 represents a group Dxe2x80x2 as defined above.
According to the invention, Y is preferably chosen from a hydrogen, chlorine, fluorine or bromine atom; a methoxy, ethoxy, propoxy, benzyloxy, phenoxy, xe2x80x94OCH2CH2OCH3; xe2x80x94OCH2CH2N(CH3)2; xe2x80x94OCH2(CO)OH, xe2x80x94OCH2(CO)OCH3, xe2x80x94OCH2(CO)OC2H5, xe2x80x94SCH2CH2CO2H or xe2x80x94NHSO2CH3 group; it being understood that Y cannot represent a group xe2x80x94NHSO2CH3 when R3 represents a hydroxyl radical.
Still more preferably, Y represents a hydrogen or chlorine atom or a methoxy, xe2x80x94OCH2(CO)OH or xe2x80x94OCH2(CO)OCH3 group.
Among the groups D, there may be mentioned, by way of example, the imidazolinium, thiazolinium, oxazolinium, pyrrolinium, 1,2,3-triazolinium, 1,2,4-triazolinium, isoxazolinium, isothiazolinium, imidazolidinium, thiazolidinium, pyrazolinium, pyrazolidinium, oxazolidinium, pyrazoltriazolinium, pyrazoloimidazolinium, pyrrolotriazolinium, pyrazolopyrimidinium, pyrazolopyridinium, pyridinium, pyrimidinium, pyrazinium, triazinium, benzoimidazolinium, benzoxazolinium, benzothiazolinium, indolinium, indolidinium, isoindolinium, indazolinium, benzotriazolinium, quinolinium, tetrahydroquinolinium, benzoimidazolidinium, benzopyrimidinium, tetra(C1-C4)-alkylammonium, polyhydroxytetra (C1-C4) alkylammonium, dialkylpiperidinium, dialkylpyrrolidinium, dialkylmorpholinium, dialkylthiomorpholinium, dialkylpiperazinium, azepinium and 1,4-diazabicyclo-[2.2.2]octanium groups.
Still more preferably, D represents a 3-methylimidazolidinium-1-yl, 3-(2-hydroxyethyl)imidazolidinium-1-yl, 1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, N-(C1-C4)alkylpyridin-2-yl, N-(C1-C4)alkylpyridin-3-yl, N-(C1-C4)alkylpyridin-4-yl, N-(2-hydroxyethyl)pyridin-2-yl, N-(2-hydroxyethyl)pyridin-3-yl, N-(2-hydroxyethyl)pyridin-4-yl, pyridin-1-yl, tri(C1-C4)alkylammonium-N-yl, 1-methylpiperidinium-1-yl, thiazolinium-3-yl or 1,4-dimethylpiperazinium-1-yl groups.
Among the compounds of formula (I), there are particularly preferred those in which:
i)
R1 represents a hydrogen atom;
R2 represents a group xe2x80x94D1, xe2x80x94Exe2x80x94D1, xe2x80x94Oxe2x80x94Exe2x80x94D1, xe2x80x94NHxe2x80x94Exe2x80x94D1, as defined above; or a radical chosen from the group (G4) consisting of a methyl, methoxymethyl, 2-carboxyethyl, methoxy, amino, ethylamino or 1-pyrrolidinyl radical;
R3 represents a hydroxyl, amino or methylamino radical; a group xe2x80x94NH(CO)R20 in which R20 represents one of the radicals listed in the group (G4) defined above; a methanesulphonylamino, ethanesulphonylamino or dimethylaminosulphonylamino group; a group xe2x80x94Oxe2x80x94Exe2x80x94D2, xe2x80x94NHxe2x80x94Exe2x80x94D2, xe2x80x94NH(CO)xe2x80x94D2, xe2x80x94NH(CO)xe2x80x94Exe2x80x94D2, xe2x80x94NH(CO)Oxe2x80x94Exe2x80x94D2, xe2x80x94NH(CO)NHxe2x80x94Exe2x80x94D2 or xe2x80x94NH(SO2)xe2x80x94Exe2x80x94D2, as defined above;
R4 represents a hydrogen or chlorine atom, or a methyl group;
R5 represents a hydrogen, chlorine or fluorine atom, or a methyl group;
Y represents a hydrogen or chlorine atom; a methoxy or xe2x80x94OCH2(CO)OCH3 group; it being understood that at least one of the groups R2 and R3 contains a group Z;
ii)
R1 represents a hydrogen atom;
R2 represents a group xe2x80x94D1, xe2x80x94Exe2x80x94D1, xe2x80x94Oxe2x80x94Exe2x80x94D1 or xe2x80x94NHxe2x80x94Exe2x80x94D1, as defined above; or one of the radicals listed in the group (G4) defined above;
R3 represents a hydrogen atom; or a methyl radical;
R4 represents a hydroxyl, amino, methylamino, methanesulphonylamino, ethanesulphonylamino or dimethylaminosulphonylamino radical; a group xe2x80x94NH(CO)R21 in which R21 represents one of the radicals listed in the group (G4) defined above; or a group xe2x80x94Oxe2x80x94Exe2x80x94D3, xe2x80x94NHxe2x80x94Exe2x80x94D3, xe2x80x94NH(CO)xe2x80x94D3, xe2x80x94NH(CO)xe2x80x94Exe2x80x94D3, xe2x80x94NH(CO)Oxe2x80x94Exe2x80x94D3, xe2x80x94NH(CO)NHxe2x80x94Exe2x80x94D3 or xe2x80x94NH(SO2)xe2x80x94Exe2x80x94D3, as defined above;
R5 represents a hydrogen, chlorine or fluorine atom; or a methyl, methoxy or methylamino group;
Y represents a hydrogen or chlorine atom; a methoxy or xe2x80x94OCH2(CO)OCH3 group; it being understood that at least one of the groups R2 and R4 contains a group Z;
iii)
R1 represents a hydrogen atom;
R2 represents one of the radicals listed in the group (G4) defined above; or a group xe2x80x94D1, xe2x80x94Exe2x80x94D1, xe2x80x94Oxe2x80x94Exe2x80x94D1, xe2x80x94NHxe2x80x94Exe2x80x94D1, as defined above;
R3 represents a hydrogen atom; or a methyl radical;
R4 represents a hydrogen or chlorine atom; a methyl radical; or a methoxy or methylamino group;
R5 represents a group xe2x80x94NH(CO)R22 in which R22 represents one of the radicals listed in the group (G4) defined above; or a group xe2x80x94Oxe2x80x94Exe2x80x94D4, xe2x80x94NHxe2x80x94Exe2x80x94D4, xe2x80x94NH(CO)xe2x80x94D4, xe2x80x94NH(CO)xe2x80x94Exe2x80x94D4, xe2x80x94NH(CO)Oxe2x80x94Exe2x80x94D4 or xe2x80x94NH(CO)NHxe2x80x94Exe2x80x94D4, as defined above;
Y represents a hydrogen or chlorine atom; or a methoxy or xe2x80x94OCH2(CO)OCH3 group; it being understood that at least one of the groups R2 and R5 contains a group Z;
iv)
R1 represents a hydrogen atom;
R2 represents a group xe2x80x94D1, xe2x80x94Exe2x80x94D1, xe2x80x94Oxe2x80x94Exe2x80x94D1 or xe2x80x94NHxe2x80x94Exe2x80x94D1, as defined above;
R3 represents a hydrogen atom; or a methyl radical;
R4 represents a hydrogen or chlorine atom; or a methyl radical;
R5 represents a hydrogen, chlorine or fluorine atom; or a methyl group;
Y represents a hydrogen or chlorine atom; or a methoxy or xe2x80x94OCH2(CO)OCH3 group.
Among the compounds of formula (I) above, there may be mentioned most particularly:
3-[(2-Hydroxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3-(2-(3-methyl-1H-imidazol-3-ium-1-yl)acetylamino)phenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium dichloride;
3-[(2-Hydroxy-4-(2-(3-methyl-1H-imidazol-3-ium-1-yl)acetylamino)phenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium dichloride;
3-[(2-Hydroxy-4-methylphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-aminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methyl-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-amino-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-acetylamino-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methoxycarbonylamino-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-acetylamino-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-methoxycarbonylamino-6-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methyl-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-amino-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-acetylamino-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methoxycarbonylamino-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-acetylamino-6-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-methoxycarbonylamino-6-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-6-aminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-6-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4,6-diaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-acetylamino-6-aminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3,5-dichloro-4-methylphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3,5-dichloro-4-aminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3,5-dichloro-4-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3,5-dichloro-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
1-[(2-Hydroxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3-(2-(pyridinium-1-yl)acetylamino)phenylcarbamoyl)methyl]pyridinium dichloride;
1-[(2-Hydroxy-4-(2-(pyridinium-1-yl)acetylamino)phenylcarbamoyl)methyl]pyridinium dichloride;
1-[(2-Hydroxy-4-methylphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-aminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methyl-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-amino-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-acetylamino-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methoxycarbonylamino-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-acetylamino-6-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-methoxycarbonylamino-6-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methyl-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-amino-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-acetylamino-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methoxycarbonylamino-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-acetylamino-6-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-methoxycarbonylamino-6-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-6-aminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-6-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4,6-diaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-acetylamino-6-aminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-methylphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-aminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-methoxycarbonylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3-(2-(1,4-dimethylpiperazin-1-ium-1-yl)acetyl)aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium dichloride;
1-[(2-Hydroxy-4-(2-(1,4-dimethylpiperazin-1-ium-1-yl)acetyl)aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium dichloride;
1-[(2-Hydroxy-4-methylphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methyl-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperaziln-1-ium chloride;
1-[(2-Hydroxy-4-amino-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-acetylamino-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methoxycarbonylamino-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-acetylamino-6-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-methoxycarbonylamino-6-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methyl-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-amino-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-acetylamino-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methoxycarbonylamino-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-acetylamino-6-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-methoxycarbonylamino-6-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-6-aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-6-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4,6-diaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-acetylamino-6-aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-methylphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride; and their addition salts with an acid.
The compound(s) of formula (I) in accordance with the invention and/or the or their addition salt(s) with an acid preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dyeing composition and still more preferably from 0.005 to 6% by weight approximately of this weight.
The nature of the oxidation base(s) which can be used in the dyeing composition in accordance with the invention is not critical. They are preferably chosen from the oxidation bases conventionally used in oxidation dyeing and among which there may be mentioned in particular para-phenylenediamines, bisphenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
Among the para-phenylenediamines, there may be mentioned more particularly by way of example para-phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(xcex2-hydroxyethyl)-para-phenylenediamine, 4-N,N-bis(xcex2-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(xcex2-hydroxyethyl)amino-2-chloroaniline, 2-xcex2-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(xcex2-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N,N-(ethyl-xcex2-hydroxyethyl)-para-phenylenediamine, N-(xcex2,xcex3-dihydroxypropyl)-para-phenylenediamine, N-(4xe2x80x2-aminophenyl)-para-phenylenediamine, N-phenyl-para-phenylenediamine, 2-xcex2-hydroxyethyloxy-para-phenylenediamine, 2-xcex2-acetylaminoethyloxy-para-phenylenediamine, N-(xcex2-methoxyethyl)-para-phenylenediamine, and their addition salts with an acid.
Among the para-phenylenediamines mentioned above, there are most particularly preferred para-phenylenediamine, para-tolylenediamine, 2-isopropyl-para-phenylenediamine, 2-xcex2-hydroxyethyl-para-phenylenediamine, 2-xcex2-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis(xcex2-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine, 2-xcex2-acetylaminoethyloxy-para-phenylenediamine, and their addition salts with an acid.
Among the bisphenylalkylenediamines, there may be mentioned more particularly by way of example N,Nxe2x80x2-bis(xcex2-hydroxyethyl)-N,Nxe2x80x2-bis(4xe2x80x2-aminophenyl)-1,3-diaminopropanol, N,Nxe2x80x2-bis(xcex2-hydroxyethyl)-N,Nxe2x80x2-bis(4xe2x80x2-aminophenyl)ethylenediamine, N,Nxe2x80x2-bis(4-aminophenyl)-tetramethylenediamine, N,Nxe2x80x2-bis(xcex2-hydroxyethyl)-N,Nxe2x80x2-bis(4-aminophenyl)tetramethylenediamine, N,Nxe2x80x2-bis(4-methylaminophenyl)tetramethylenediamine, N,Nxe2x80x2-bis(ethyl)-N,Nxe2x80x2-bis(4xe2x80x2-amino-3xe2x80x2-methylphenyl)ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and their addition salts with an acid.
Among the para-aminophenols, there may be mentioned more particularly by way of example para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(xcex2-hydroxyethylaminomethyl)phenol, 4-amino-2-fluorophenol, and their addition salts with an acid.
Among the ortho-aminophenols, there may be mentioned more particularly by way of example 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and their addition salts with an acid.
Among the heterocyclic bases, there may be mentioned more particularly by way of example pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
Among the pyridine derivatives, there may be mentioned more particularly the compounds described for example in Patents GB 1,026,978 and GB 1,153,196, such as 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(xcex2-methoxyethyl)amino-3-amino-6-methoxypyridine, 3,4-diaminopyridine, and their addition salts with an acid.
Among the pyrimidine derivatives, there may be mentioned more particularly the compounds described for example in German Patent DE 2,359,399 or Japanese Patents JP 88-169,571 and JP 91-10659 or Patent Application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and the pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2,750,048 and among which there may be mentioned pyrazolo[1,5-a]pyrimidine-3,7-diamine; 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; pyrazolo[1,5-a]pyrimidine-3,5-diamine; 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine; 3-aminopyrazolo[1,5-alpyrimidin-7-ol; 3-aminopyrazolo[1,5-alpyrimidin-5-ol; 2-(3-amrinopyrazolo[1,5-alpyrimidin-7-ylamino)ethanol, 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino) ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl) (2-hydroxyethyl)amino]ethanol, 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxyethyl)amino]ethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidin-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 3-amino-5-methyl-7-imidazolylpropylaminopyrazolo[1,5-a]pyrimidine, their tautomeric forms, when a tautomeric equilibrium exists, and their addition salts with an acid.
Among the pyrazole derivatives, there may be mentioned more particularly the compounds described in Patents DE 3,843,892, DE 4,133,957 and Patent Applications WO 94/08969, WO 94/08970, FR-A-2,733,749 and DE 195 43 988 such as 4,5-diamino-1-methylpyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4xe2x80x2-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(xcex2-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4xe2x80x2-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole, 4,5-diamino-3-methyl-1-isopropylpyrazole, 4-amino-5-(2xe2x80x2-aminoethyl)amino-1,3-dimethylpyrazole, 3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole, 3,5-diamino-4-(xcex2-hydroxyethyl)amino-1-methylpyrazole, and their addition salts with an acid.
According to the invention, the dyeing compositions containing one or more para-phenylenediamines and/or one or more heterocyclic oxidation bases are particularly preferred.
The oxidation base(s) preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dyeing composition, and still more preferably from 0.005 to 6% by weight approximately of this weight.
The dyeing composition in accordance with the invention may also contain, in addition to the compound(s) of formula (I) above, one or more additional couplers which may be chosen from the couplers conventionally used in oxidation dyeing and among which there may be mentioned in particular meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives and pyrazolones, and their addition salts with an acid.
These couplers are more particularly chosen from 2-methyl-5-aminophenol, 5-N-(xcex2-hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene, 2,4-diamino-1-(xcex2-hydroxyethyloxy)benzene, 2-amino-4-(xcex2-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, xcex1-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine, 1-H-3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one, and their addition salts with an acid.
When they are present, these additional couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dyeing composition and still more preferably from 0.005 to 5% by weight approximately of this weight.
In general, the addition salts with an acid which can be used in the context of the dyeing compositions of the invention (compounds of formula (I), oxidation bases and additional couplers) are chosen in particular from hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates.
The medium appropriate for dyeing (or carrier) generally consists of water or of a mixture of water and at least one organic solvent for solubilizing the compounds which might not be sufficiently soluble in water. By way of organic solvent, there may be mentioned for example lower C1-C4 alkanols such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, monomethyl ether of propylene glycol, monoethyl ether and monomethyl ether of diethylene glycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof.
The solvents may be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dyeing composition, and still more preferably between 5 and 30% by weight approximately.
The pH of the dyeing composition in accordance with the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or alkalinizing agents normally used in dyeing keratinous fibres.
Among the acidifying agents, there may be mentioned, by way of example, inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid and sulphonic acids.
Among the alkalinizing agents, there may be mentioned, by way of example, aqueous ammonia, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and the compounds of the following formula (V): 
in which W is a propylene residue which is unsubstituted or substituted with a hydroxyl group or a C1-C6 alkyl radical; R23, R24, R25 and R26, which are identical or different, represent a hydrogen atom, a C1-C6 alkyl or C1-C6 hydroxyalkyl radical.
The oxidation dyeing compositions in accordance with the invention may also contain at least one direct dye, in particular for modifying the shades or enriching them with glints.
The dyeing composition in accordance with the invention may also contain various adjuvants, conventionally used in hair dyeing compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as for example modified or unmodified, volatile or nonvolatile silicones, film-forming agents, ceramides, preservatives, opacifying agents.
Of course, persons skilled in the art will be careful to choose this or these possible additional compound(s) such that the advantageous properties which are intrinsically attached to the oxidation dyeing composition in accordance with the invention are not, or not substantially, impaired by the addition(s) envisaged.
The dyeing composition according to the invention may be provided in various forms, such as in the form of liquids, creams, gels, or in any other form appropriate for dyeing keratinous fibres, and in particular human hair.
The subject of the invention is also a method of oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, using the dyeing composition as defined above.
According to this method, at least one dyeing composition as defined above is applied to the fibres, the colour being developed at acidic, neutral or alkaline pH with the aid of an oxidizing agent which is added just at the time of use to the dyeing composition or which is present in an oxidizing composition applied simultaneously or sequentially.
According to a preferred embodiment of the dyeing method of the invention, the dyeing composition described above is preferably mixed, at the time of use, with an oxidizing composition containing, in a medium appropriate for dyeing, at least one oxidizing agent present in a sufficient quantity to develop a colour. The mixture obtained is then applied to the keratinous fibres and allowed to act for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which they are rinsed, washed with shampoo, rinsed again and dried.
The oxidizing agent may be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratinous fibres, and among which there may be mentioned hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, and enzymes such as peroxidases, laccases, tyrosinases and oxidoreductases among which there may be mentioned in particular pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases and uricases.
The pH of the oxidizing composition containing the oxidizing agent as defined above is such that after mixing with the dyeing composition, the pH of the resulting composition applied to the keratinous fibres preferably varies between 3 and 12 approximately, and still more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or alkalinizing agents normally used for dyeing keratinous fibres and as defined above.
The oxidizing composition as defined above may also contain various adjuvants conventionally used in hair-dyeing compositions and as defined above.
The composition which is finally applied to the keratinous fibres may be provided in various forms, such as in the form of liquids, creams, gels or in any other form appropriate for dyeing keratinous fibres, and in particular human hair.
Another subject of the invention is a multicompartment device or dyeing xe2x80x9ckitxe2x80x9d or any other multicompartment packaging system in which a first compartment contains the dyeing composition as defined above and a second compartment contains the oxidizing composition as defined above. These devices may be equipped with a means which makes it possible to deliver the desired mixture to the hair, such as the devices described in patent FR-2,586,913 in the name of the applicant.
Some compounds of formula (I) are novel per se and thereby constitute another subject of the invention. These novel compounds, as well as their addition salts with an acid, correspond to the following formula (I)xe2x80x2: 
in which Rxe2x80x21, Rxe2x80x22, Rxe2x80x23, Rxe2x80x24, Rxe2x80x25 and Y can have the same meanings as those indicated above for R1, R2, R3, R4, R5 and Y, in which at least one of the groups Rxe2x80x21 to Rxe2x80x25 represents a group Zxe2x80x2 which can have the same meanings as those indicated above for the group Z; excluding the following compounds: 
in which R represents a 4-methyl-C6H4, 4-chloro-C6H4 or 2-ethoxy-C6H4 radical 
which are known in the photographic or medical field, see in particular the documents Bull. Soc. Chim. Fr. (1966), 400-3; Bull. Soc. Chim. Fr. (1969), 4390-4; Zh. Org. Khim. (1972), 8, 2429-31; Des. Monomers Polym. (1998), 1, 15-36; and the patent applications EP 0,303,301; JP 07,271,075 and EP 0,790,240.
Among the compounds of formula (Ixe2x80x2) in accordance with the invention, there may be mentioned in particular:
3-[(2-Hydroxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3-(2-(3-methyl-1H-imidazol-3-ium-1-yl)acetylamino)phenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium dichloride;
3-[(2-Hydroxy-4-(2-(3-methyl-1H-imidazol-3-ium-1-yl)acetylamino)phenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium dichloride;
3-[(2-Hydroxy-4-methylphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-aminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methyl-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-amino-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-acetylamino-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methoxycarbonylamino-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-acetylamino-5-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-methoxycarbonylamino-6-chlorophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methyl-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-amino-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-acetylamino-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-methoxycarbonylamino-5-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-acetylamino-6-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(3-Hydroxy-4-methoxycarbonylamino-6-methoxyphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-6-aminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-6-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4,6-diaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-4-acetylamino-6-aminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3,5-dichloro-4-methylphenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3,5-dichloro-4-aminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3,5-dichloro-4-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3,5-dichloro-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(2-Hydroxy-3-acetylaminophenylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
1-[(2-Hydroxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3-(2-(pyridinium-1-yl)acetylamino)phenylcarbamoyl)methyl]pyridinium dichloride;
1-[(2-Hydroxy-4-(2-(pyridinium-1-yl)acetylamino)phenylcarbamoyl)methyl]pyridinium dichloride;
1-[(2-Hydroxy-4-methylphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-aminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methyl-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-amino-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-acetylamino-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methoxycarbonylamino-5-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-acetylamino-6-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-methoxycarbonylamino-6-chlorophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methyl-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-amino-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-acetylamino-5-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-methoxycarbonylamino-5-methoxylphenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-acetylamino-6-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(3-Hydroxy-4-methoxycarbonylamino-6-methoxyphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-6-aminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-6-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4,6-diaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-4-acetylamino-6-aminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-methylphenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-aminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-methoxycarbonylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxy-3-acetylaminophenylcarbamoyl)methyl]pyridinium chloride;
1-[(2-Hydroxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3-(2-(1,4-dimethylpiperazin-1-ium-1-yl)acetyl)aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium dichloride;
1-[(2-Hydroxy-4-(2-(1,4-dimethylpiperazin-1-ium-1-yl)acetyl)aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium dichloride;
1-[(2-Hydroxy-4-methylphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methyl-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-amino-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-acetylamino-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methoxycarbonylamino-5-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-acetylamino-6-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-methoxycarbonylamino-6-chlorophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methyl-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-amino-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-acetylamino-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-methoxycarbonylamino-5-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-acetylamino-6-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(3-Hydroxy-4-methoxycarbonylamino-6-methoxyphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-6-aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-6-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4,6-diaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-4-acetylamino-6-aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-methylphenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-aminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3,5-dichloro-4-methoxycarbonylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(2-Hydroxy-3-acetylaminophenylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride; and their addition salts with an acid.
The addition salts with an acid of the compounds of formula (Ixe2x80x2) may be in particular chosen from hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates.
These novel compounds of formula (Ixe2x80x2) may be prepared according to methods well known in the state of the art and described for example in patent applications or patents FR-A-1,596,879; BE 816,674; EP 0,579,204; DE 2,846,931; JP-54-115230; GB 2,070,000; DE 3,027,128; EP 0,065,874; EP 0,115,194; EP 0,079,141; EP 0,081,321; DE 3,246,238; EP 0,168,729; DE 3,414,051; JP-59-059656; FR-A-2,575,470; EP-0,193,051; JP-63-208562; JP-62-173469; JP-62-108859; JP-62-173469; DD253997; DE 3,641,825, JP-63-208562; DE 3,621,215; JP-01-249739; JP-64-002045; JP-02-255674; JP-01-032261; JP-02-255674; EP 0,608,896; WO 94/19316; JP-09-169705; EP 0,790,240; as well as in the documents Res. Discl. (1981), 202, 76-8; Synthesis (1982), 940-2, Res. Discl. (1983), 235, 352-3; Res. Discl. (1984), 247, 554-6; Res. Discl. (1985), 251, 134-9; Chem. Ind. (Dekker) (1992), 47 (Catal. Org. React.), 147-51; and J. Med. Chem. (199) 4062-79.
The subject of the invention is finally the use of the compounds of formula (Ixe2x80x2) as coupler for the oxidation dyeing of keratinous fibres and in particular human keratinous fibres such as hair.
The following examples are intended to illustrate the invention without limiting the scope thereof as a result.